Bars We Love: The Esquire Tavern, San Antonio

Drinking is easy. Finding the right bar, not so easy. We’re here to help. As a public service to all of you thirsty explorers, every week we highlight the best bars in America and tell you what makes them so damn great. This week we’ve got a Tejas tavern that opened the day Prohibition was repealed.

WHAT TO ORDER (NEWBIES): Texecutioner: Espadín mezcal, Xtabentún liqueur, Cocchi Americano and grapefruitWHAT TO ORDER (REGULARS): Mezcal and a pint of Freetail

WHY WE LOVE IT: In 2006 the San Antonio police station received more than 300 calls about The Esquire Tavern. The 73-year-old River Walk bar had become a seedy and damn near dangerous watering hole and it was forced to close down. Five years later the tavern reopened, under new ownership, and is now widely considered one of the best craft cocktail bars in the state. “People still come in and tell stories about it,” beverage director Houston Eaves says. “Last weekend someone told me that he used to come in here with his grandparents in the ’50s. His grandpa would play pool in the back and he would get the beers from the bar.”

The original Esquire Tavern opened on Repeal Day, 1933, and was named so due to its centralized location downtown. “We’re really close to the courthouse,” Eaves says. “So we got the courthouse crowd: lawyers, judges, politicos, and also plaintiffs and defendants. It’s always catered to all different classes.” The bar still attracts a large spectrum of customers and even has its original seating and whiskey-soaked bar top—a 100+-foot-long slab of mahogany—which were lovingly restored in 2011.

Kody Melton

Today the bar is known less for its sordid past and more for its swanky, creative cocktails, which are often inspired by song lyrics. Take for instance the Snakeskin Suit, Alligator Boot cocktail (taken from The Clash’s “Koka Kola”). It includes firey mezcal, aquavit (a dill-flavored spirit) and leafy kale. The winters in San Antonio are mild, so the bar never really resorts to heavy fall drinks. But in the summer, bright and refreshing cocktails are essential for cutting through the heat and quenching the thirst of parched San Antonians.

“Everything we do is spirit-forward, so even when it’s a light drink, we are still trying to showcase the spirit,” Eaves says. “We don’t shy away from booze. We like to let people know they are consuming drinks.” The bold cocktails can be deceptive to tourists who aren’t used to boozy margaritas served in coupes, for example. They’ll have two and need help getting back to their hotels. But for the regulars and industry folks who frequent The Esquire, most of them are looking for one thing: mezcal.

The Esquire has more than 100 different kinds of mezcal at the bar, mostly because of Eaves’ personal interest in the Mexican spirit. “We’re so deeply Mexican and Mexican-American in San Antonio that the culture that is happening in Mexico right now is happening in San Antonio too,” he says. “A lot of people come from the mindset that mezcal is the campesino (peasant) drink, or the drink for poor people.” But as mezcal has exploded in popularity in the U.S. over the past five years or so, the people of San Antonio have been quick to embrace it. “You see the same thing happening in Mexico City and Oaxaca, where now mezcal is really being appreciated and people are understanding what an amazing cultural treasure it is.”

Eaves passion for agave extends outside of the bar. He is a member of the Tequila Interchange Project, a non-profit organization composed of bartenders and academics who advocate for sustainable agricultural practices and preservation of tradition in Mexican distillation. In January he will lead an in-depth session at the San Antonio Cocktail Conference on the American bartender’s perspective on mezcal culture.

Kody Melton

Alyson Sheppard is the resident hangover specialist at Playboy.com. Find her on Twitter: @amshep